


It's Your Money, Your Choice.

by Dolavine



Series: 30 days of porn OTP fic challenge [4]
Category: Supernatural
Genre: Anal Sex, Bottom Dean, Hooker Sam, M/M, Man handling, Rough Kissing, Rough Sex, Sex workers, Top Sam
Language: English
Status: Completed
Published: 2014-07-22
Updated: 2014-07-22
Packaged: 2018-02-10 00:01:15
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,337
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2003124
Author URL: https://archiveofourown.org/users/Dolavine/pseuds/Dolavine
Summary: <blockquote class="userstuff">
              <p>Dean Smith hires a hooker for the first time; it turns out to be his office crush, Sam Wesson.</p>
            </blockquote>





	It's Your Money, Your Choice.

**Author's Note:**

> Day 4 of 30 Days of porn, Otp. Prompt: Sex Workers

Dean’s not in the habit of calling a prostitute for sex but he’s been having a bit of a dry spell lately because long work days makes for a lack of dating time.

Tonight, he’s horny and lonely, so he decides to call an escort place that a coworker suggested and then told him, _get laid, you’ll feel better._

The operator asks him if he has any preferences to what he’d like; as in- body, hair, or height.

“I like tall, six foot or more, longish hair, and dimples if that is possible. Buff body, not over muscular but long and built.” He has Sam, the tech support guy, in mind as he’s describing what he’s attracted to. It’s not like he hasn’t masturbated to the thought of him before… or every time since he met him. 

The particulars are worked out, address, name- Dean doesn’t want to give his real name so he says Ross- his middle name, and price- which is charged to his credit card immediately, now all he has to do is wait.

Sam’s relaxing when his cell rings- he answers it. It’s his second job. Tech support doesn’t really pay enough to cover the bills and have extra left over, so he’s taken on a pretty good paying evening job as a call boy. He can make his own hours and he likes that, plus the tips are great.

He gets an address- which sounds familiar but he’s not really sure, the name Ross- which he’s sure he doesn’t know, and is told it’s an ASAP job. 

He showers, doesn’t shave, splashes on his favorite scent of cologne then dresses. He was told it’s a casual dress, so he puts on his favorite skinny jeans, a nice crisp blue button down and his Converse sneakers. He checks himself out in the mirror; his hair is still damp and pushed back off of his face and he’s pretty sure that he’s ready to go. He grabs several condoms from the top drawer of his dresser and stuffs them into his pocket. Empties all of the cash and credit cards from his wallet and tucks his driver’s license into a secret slot behind the card holder. He’s been robbed before and it isn’t happening again. 

As he gets closer to the address he’s sure he’s been here before. 

He strolls through the lobby to the elevator. The ride up is almost tedious as it climbs the 14 floors. The bell finally dings and the doors open. He steps into the well lit hallway and makes his way to the apartment number.

Dean’s nervous, he’s never done anything like this- okay he has but it was under completely different circumstances and well, he was in Las Vegas. 

He’s showered, put on his favorite old comfy rock t-shirt, worn jeans and is going barefoot. The wine is breathing- he’s not sure if wine is acceptable but he might need a drink to loosen up, either way, the wine is breathing, and he’s put on some soft jazz music for a little atmosphere.

Sam can’t shake the feeling that he knows this apartment building. He knocks on the green metal door.

Dean hears a knock at the door and goes to answer it. He looks out the peep hole but only sees the chin of the man outside. He smiles because he’s that tall and it will make it much easier to close his eyes and pretend that it’s Sam.

He takes a deep breath to calm his nerves and opens the door.

The sound of the latch clicks and Sam stands tall preparing to see his _date_ for tonight.

Dean’s eyes meet with the man’s on the other side of the door. He’s shocked, speechless and utterly flabbergasted.

Sam smiles a knowing grin as the pieces all fall into place and he remembers exactly how he knows this apartment building. “Dean,” he says it with a reassured tone.

“Sam?” Dean’s tone is slightly bewildered and questioning. He stares at him for a few brief seconds before Sam’s voice breaks his trance.

“Are you going to invite me in?”

“Uh, yeah, sure, come on in.” He steps out of the way so Sam can enter, still staring at him like he can’t believe it.

“I thought I recognized the building when I came in, but just couldn’t place it.” Sam looks around, familiarizing himself with the apartment again.

“Uh, yeah.” Dean keeps stammering. He’s not sure if this is really what he had in mind when he ordered the Sam-a-like, because he never expected to actually receive the actual Sam Wesson, in the oh so sexy flesh. “Wine?” he asks pouring himself a big glass and downing it before refilling and offering one to Sam.

“Absolutely,” He leans over the counter. “So, I thought, you weren’t into,” he moves his hand up and down to gesture the fact that he’s a man. “Guys.” 

He hands Sam the wine and nervously drinks from his own glass. “I never said I wasn’t into guys, I merely suggested that I wasn’t into you. You know, because you were acting weird on the elevator and all.” He chugs his glass of wine and pours another before stepping out of the kitchen into the living room area.

Sam sits down on the sofa and sips his wine. “So, are you attracted to me now, because they usually ask for what you’d like in your date, unless you’re a regular customer and I’m just filling in on short notice?” He smiles a flirtatious grin.

“No, no.” Dean drinks a little more wine. “I’m a virgin, I mean, not a virgin, a new customer- not that I’m going to be a regular customer.” He sits down at the other end of the sofa and takes several more swallows of his wine.

“Do you even taste that wine?” Sam laughs then scoots in closer to Dean.

Dean looks at his half empty third glass of wine in less than fifteen minutes. “Not really.” He admits. “I’m a little nervous.” 

Sam slides up against Dean and puts his hand on Dean’s thigh. “You don’t need to be nervous. We know each other and I’ll tell you a little secret.” He leans in and ghosts his mouth against Dean’s ear. “I already like you; you could have had me for free.” He slips his tongue out and caresses the shell of Dean’s ear before pulling away.

Dean shudders, his skin is covered in goose-bumps and his heart rate just shot up to severely high levels. He swallows thickly then takes another drink of his wine as he just stares straight ahead trying to process what just happened. “Really?” he manages to croak out, like he can’t believe it.

“Really,” Sam confirms. “But, you’ve already paid for my services, so… whenever you’re ready, just make the first move.” He leans back and swings his feet up to prop them over Dean’s lap. 

Dean’s brain is ticking with the idea of having bought his first experience with Sam. That Sam is for sale, for rent, for use. He puts down his wine and turns to face him. “So, you’re a seasoned professional?” he licks his lips at the question.

“I wouldn’t say seasoned, but, I’ve had my share of pay dates.” Sam can see the wheels turning behind Dean’s watery green eyes.

He’s not sure if it’s the wine kicking in or the fact that the thought of owning Sam for however long seven hundred dollars buys you, but he’s feeling flushed and his dick is starting to pay much more attention to the situation.

“Do I get anything I want?” Dean runs his fingers over the tips of Sam’s sneakers as he looks over at him from under his brow.

Sam smirks as he bites his lower lip, his eyes get an impish glint as they narrow and bead in on Dean. “Anything is a pretty loose word.” He runs his tongue over his bottom lip then takes a sip of wine never breaking eye contact with Dean.

“Sex- I mean, sexually. Can we do something that I’ve always wanted to do or do you have boundaries?” He bites the inside of his mouth nervously as he works his fingers up under Sam’s tight jeans to his calve and swirls them through the fine hairs over his shinbone.

“It’s your money, your time and your choice.” He sits up and leans forward. “I have quite a repertoire of kinks under my belt.” He runs his fingertips down the side of Dean’s face. It’s a gentle caress that ends at his chin as he pulls him in for a soft kiss. 

It’s a mutual caress of lips. It’s sensual but not passionate. They’re testing the waters, tasting each other and building the need between them.

 

Dean pulls back, his eye still closed as he licks the lingering wetness from his lips. When he opens his eyes, Sam’s smiling at him, his dimples so deep he could lose a finger in one of them if he were to poke it. “I’d like you to manhandle me.” He swallows hard, his nerves getting the best of him after he says it. He’s never had the guts to ask for it before but if he can have what he wants, -this is what he wants.

“You mean, do it rough or throw you around?” Sam needs to clarify so that he’s not overstepping any boundaries in this transaction. 

“Yes.” Dean says enthusiastically. 

“Yes, rough me up or yes throw me around?” 

“Both. Do it rough and throw me around. Basically, use me.” He bites his lower lip and gives Sam a seductive look.

“I can do that.” He tightens his grip on Dean’s bicep as he pulls him in for another kiss, this time pushing in harder, smashing their lips together and pushing his way into Dean’s mouth with his tongue. 

It’s not polite or tender when he pulls Dean in to his body and crawls on his knees so that he has the upper hand. He leans him back on the sofa and straddles his thighs as he continues to hover over Dean and kiss him. 

Dean’s clutching onto Sam, his hands fixed firmly to Sam’s hips. “Mmmph.” He manages to make noises against Sam’s hard mouth. He wants this, has asked for it and that fact that he’s fully erect now, shows how much he **needs** this.

Sam pushes his hips into Dean’s body, grinds down, and swivels them. Dean cants his hips upward trying to press into Sam’s body but he can’t get enough pressure as Sam brushes roughly past his erection.

“Are you teasing me?” he’s pulling on Sam’s hips and staring into his eyes with desperate intent.

“Maybe.” Sam smirks, his hazel eyes darker with lustful intent. He’s enjoying this as much as Dean but he has to stay professional, this time.

Their bodies collide through denim and cotton as they writhe on the sofa as Sam nuzzles Dean’s neck. Dean’s legs are hanging off the edge and Sam’s knee is barely holding onto the framework. 

“I have a bedroom.” Dean says breathlessly as he tilts his head upward to give Sam more space to work over.

“Is it far away?” Sam’s busy working his mouth over Dean’s jaw. 

“Not really.”

“Then what are we waiting for?” Sam shifts his leg to the floor and pulls Dean up with him as he stands up. “Lead the way.” He’s still clinging to Dean; - he’s not going to let him go that easily.

Dean starts to turn but Sam pulls him back in and turns around so that he’s the one facing backwards. 

“How is this supposed to work?” He’s still has his arms wrapped around Sam.

“You lead, I’ll follow. It’s a dance.” He runs his fingers up the back of Dean’s neck and tugs lightly at the short spikes of hair. 

Dean smiles before starting to move forward. Sam mirrors his steps, his hands still roaming Dean’s body, and his mouth is still sucking at Dean’s neck. 

They make it across the room when Sam’s back hits the wall. He starts to laugh. “You are a terrible driver.”

“I’m a little bit distracted.” 

“I’ll see what I can do about that.” Sam’s voice takes a darker tone, his fingers grip into  
Dean’s flanks and he turns the tables on them.

Sam’s hands slide around Dean’s abdomen and down to the hem of his t-shirt. He smiles slyly as his fingers dip underneath to the warm taut flesh underneath. “Firm.” He licks his lips as he continues his task. His hand moves up over the thick ripples of Dean’s well muscled six-pack, then up and over the hard mounds of his pectorals. “Nice.” Sam’s one word descriptions sound lascivious as they roll thickly off of his tongue. 

He’s managed to ruck Dean’s t-shirt up over his chest and has it bunched up at his neck where he takes both hands pulls it taunt then holds it tight over the base of Dean’s throat. 

Dean gasps at the feelings, his heart pounds with excitement as Sam shoves him against the wall and holds him there by his neck using only the fabric of his shirt. He closes his eyes and gives Sam all of the control.

“Hold still.” Sam commands as he leans down and flicks his tongue over one of the hard perky nipples. 

Dean flinches and pulls his abs tight at the sensation. 

Sam smiles at the reaction. He pulls the shirt up and over Dean’s head then pulls it furiously off of his arms. He gawks at Dean’s hard muscles and soft freckled skin. He smoothes his hands over the hard lines of muscle, down to the waist of Dean’s jeans and quickly undoes the buttons. His hands are skilled as he works them open with ease. 

Dean’s watching him, his excitement growing with each touch. His cock is throbbing as he feels the buttons come open and loosen the tight confines pushing against it. It’s a relief until he feels Sam’s hand snake inside of his boxers and take a firm grip of it. He arches his back at the intense pleasure. “Fuck.” He gasps, throws his head back against the wall and closes his eyes as he lets it wash over him.

Sam just smiles and begins to stroke roughly up and down Dean’s big cock. His free hand pulls down both Dean’s boxers and jeans to his knees exposing the sensitive skin as he pulls on Dean’s leaking cock.

His thumb caresses the head, smearing the oozing precome over the top with each stroke. The foreskin slips over the cap then loosely over the shaft as Dean bucks into Sam’s hand.

“So fucking good.” It’s a whimper. Dean’s eyes move down to Sam’s hand and he can’t do anything but clutch the wall and rock into Sam’s grip.

Sam claims Dean’s mouth. He presses into Dean and grinds against him as he simultaneously pumps his cock. “It should be- I am a professional ya know.” He chuckles into Dean’s ear as he nibbles on the earlobe.

Sam’s hard and aching to be inside of Dean. “You have to get naked.” His words are breathy as he takes his foot and steps on the crotch of Dean’s jeans so that he can step out of them- which he does. 

“Good.” Sam rewards him by slipping two of his fingers into Dean’s mouth. “Get them good and wet.” It’s a seductive command and Dean obliges.

He sucks on the digits, his mouth gathering saliva and spreading it over the two long fingers buried inside of his mouth, stroking over his tongue. Dean loves the sensation, would love it to be Sam’s cock… _which he has yet to see and is very eager to do so_.

“That’s it, Dean, make them good and wet.” Sam’s body is tingling with the soft sucking sensations, the warm wet heat surrounding his digits and he could lose himself in the feeling very easily, give in to Dean’s mouth and shove him down to his crotch- but he won’t. 

He pulls out of Dean’s mouth and slips the hand down behind Dean’s balls and into the crease of Dean’s ass. He finds the soft tight pucker and smears it with the thick saliva. He’s circling the entrance, pushing at the tiny hole then backing away to circle it once more.

“Christ.” Dean gasps, his body is on fire and his knees are actually shaking. Sam’s methodically jerking him off as he plays with his ass. He holds on tight to Sam’s shoulders as he begins to rock and swivel his hips, pushing into both pleasurable sensations. He grabs hold of Sam’s shirt collar and pulls until the buttons give way and expose his tan muscular chest. Dean slips his hands underneath the fabric and feels the sweat glistened skin.

“You like to be fucked?” Sam whispers into his ear.

“Yeah.” Dean swallows hard, his Adam’s apple bobs under the skin of his exposed neck and Sam licks it. 

Sam pushes his finger inside of Dean’s weakening force, only going first knuckle deep and he knows he did the right thing when Dean lets out a soft relaxing moan. 

“Like that?” He asks as he twists the finger then pushes a little deeper.

“Uh, huh,” Dean’s leaning his forehead on Sam’s broad shoulder as he clings to his biceps.

Sam doesn’t even wait, without extra spit or lube of any kind he breaches Dean’s slowly relaxing hole with another finger, shoving them both in past the second knuckle and holding still as Dean gets used to the feeling of being full.

“Oh- God!” Dean exclaims. His breath hitches and his back arches at the sudden burn. He’s trying hard to relax but he’s gripping Sam’s arms so tight he might leave bruises.

“Relax.” Sam urges as he starts to move his fingers gently. Slightly thrusting with tiny movements and then twisting a little just to get him used to the feeling of being fucked. 

“Yeah.” Dean gasps, his body letting go of the rigidness, each muscle relaxing a little with each movement until he’s lax against Sam’s body, leaning against him like a rag doll. 

Sam moves in and out, feeling Dean’s hole relax and quiver for more, for something bigger to stretch it out and fill it up.

“God.” Dean says his voice soft and needy. “Need lube.” The raw burn is starting to hurt. 

“I got you.” Sam pulls a condom packet from his pocket with a small rubber vial attached to it. He slowly removes his fingers from Dean’s ass.

Dean moans, his ass feeling instantly empty and clenching to find that feeling again. 

Sam pulls his jeans down to his thighs, his hard cock falling forward and rubbing against Dean’s. 

“Shit.” Dean gasps at the sheer size of Sam’s long prick. He reaches down and touches it. “No wonder you’re a professional, with a cock like that, you’d get all the money.” He chuckles.

“Thanks.” Sam laughs. He puts the condom on with ease then slathers the small rubber vial of lube over his fingers and condom covered cock. 

He puts one of Dean’s legs over his hip. “Anchor yourself to me.” It’s a command that Dean can’t deny.

Sam smears the lube from his fingers over the crack of Dean’s ass and his relaxed hole, dipping his fingers inside to grease the entrance. 

“Holy hell.” Dean gasps at the feeling, his ass clenching to try and keep Sam trapped inside but he slips out leaving him empty again.

Sam lifts Dean’s balls and slides his well lubed cock between his thighs and over his hole. “Put your other leg up over me and hook your ankles.” He adjusts himself to hold all of Dean’s weight. 

Dean does as asked, his body now wrapped around Sam like he’s shimming up a pole. 

Sam slips his cock down the crack of Dean’s ass and pushes into the waiting hole. It goes in with ease and Dean whimpers, a sound of sheer pleasure, as he feels the head breach him. 

He shoves Dean against the wall as he cants his hips and pushes inside of him. Sam’s thrusting slowly as he builds up speed until he’s pounding shallow rapid fire thrusts into Dean’s body. 

Dean’s bouncing on Sam’s cock, slipping it in deeper with each rocking motion until he feels it bottom out and he still wants more inside of him. He’s clutching onto Sam’s shoulders, using them as leverage while Sam smashes into him with relentless force and friction. 

“Jesus!” Sam cries out, his cock pulsing and throbbing inside of Dean’s heat. His arms are wrapped as tight as he can get them around Dean’s hips as he spreads his ass cheeks wider, those long fingers digging into the soft round flesh as he tries to get every inch inside of Dean. 

He’s slamming Dean against the wall, virtually throwing him up and down on his cock and Dean’s apparently enjoying all of it because he’s grunting and moaning. His fingers dig into Sam’s shoulders before they find their way up to entwine through Sam’s long soft locks. He’s rocking his hips and his head is thrown back as he enjoys the pleasure of being fucked so vigorously. 

“Gonna… make… me come.” Dean calls out, his voice broken from the rough slamming his body is taking. His cock is trapped between them. The hot friction of their bodies moving together has him leaking a steady stream of precome. 

Sam increases the pace, their bodies colliding violently as Dean is shoved forcefully and continually against the wall with each thrust. 

Dean squeezes the nape of Sam’s neck hard, his nails biting the flesh as he comes in thick spurts between them, his body ridged with the release.

“That’s it.” Sam urges. “Come for me.” He continues to fuck into Dean, his own pleasure superseding Dean’s orgasm. 

Dean’s tight heat clenches around Sam’s cock. Sam’s moaning and grunting as he plows into Dean’s ass. He can barely stand the pool of heat swirling in his belly, the shivers of pleasure rippling up his spine as Dean continues to clench through his orgasm. 

“Fuck, yeah!” Sam cries out, his body shaking with the need to come.

It’s not long. Several more thrusts and Sam’s following Dean over the edge. His orgasm is so intense that with the final thrust he pushes Dean into the wall- literally _into_ the wall, his body making an imprint in the battered dry wall.

“Fuck.” Dean falls forward, his body limp and satiated. He leans his head on Sam’s shoulder as he continues to milk Sam’s cock with his ass muscles. 

Sam’s trying hard to continue holding Dean up. His legs are weak and he’s still buried inside of Dean. “Gonna have to climb down.” He’s breathless.

“Oh yeah sure,” Dean gathers up the strength and unhooks his legs; he lets only one down so that Sam can pull out. The soft pop of Sam’s cock as it escapes the tight ring sends shivers of pleasure up Dean’s spine. He moans with the feeling.

“God, you’re so fucking tight.” Sam nestles his mouth into Dean’s neck as he lets him finish unhooking himself. 

 

“Seems we’re a mess,” Dean chuckles then runs a finger through the cooling come on his abdomen. 

“I think my shirt is ruined.” Sam’s wiping the come off of his chest with the hem. “Got a clean one I can borrow?”

“Sure.” Dean takes his hand and leads him to the bedroom. He takes a crisp white shirt out of the closet. “You might want to clean up first.” He points to the bathroom.

“Thanks.” Sam closes the bathroom door behind himself. He pulls the condom off and throws it in the trash can. He’s looking in the mirror. His hair is a mess, his lips are bruised and swollen from the rough kissing and he’s never enjoyed having sex with a customer so much in his life. He wants to strip down and go back out there, climb into bed with Dean and cuddle him- but he can’t. He turns on the water and pulls a washcloth off of the shelf.

Dean wipes his belly and cock with a wet wipe from the pack he keeps in the nightstand. He’s still naked, his ass is still clenching softly as it begs for more of Sam’s girth. He’s sitting on the edge of the bed when Sam comes out.

Sam’s cleaned up and has put on the shirt, it’s a bit snug in the shoulders and short in the hem but its good enough to get him home. “I’ll return this tomorrow- freshly laundered of course.” He’s turning to leave when Dean stops him.

“Do you want to stay?” He’s hopeful.

Sam closes his eyes and takes a quiet breath. “There’s a charge for an overnight stay.” He doesn’t turn around.

“Oh.” Dean’s crestfallen. 

“Didn’t they explain that to you?” He still doesn’t turn around, just stands in the doorway, halfway out.

“Probably, but I didn’t think I’d be using it so I declined the charge.” He pulls the blanket over his nude body and stands up.

“Yeah.” Sam won’t look at him because he knows that if he does- he’ll stay- free of charge.

“At least let me walk you to the door.” Dean’s following him into the hallway.

They get to the door and Sam opens it, doesn’t look back- just looks down at the floor towards Dean. “Anytime you want me… you know where to find me.” He steps out of the door and walks down the hall.

**The Next Morning…**

Dean’s not even in the office ten minutes when he picks up the phone and dials an extension number.

“Tech support, Sam Wesson. How may I help you?”

“We’ll figure that out… once you’re in my office.”

The End


End file.
